It depends on what you call "non-trivial". I found answers on how to circumvent dumb macos bugs on Apple forums at least twice in the last 6 months. One related to displays, I was about to return a new USB-C monitor which wouldn't turn on. A silly issue, but it's a bug on my book, I wouldn't find the answer on the docs.
That counts! I suppose I’m lucky enough to know of more reliable resources (macadmins.org Slack is an excellent community), and so I turn to them after reading more than a couple of threads on the Apple Support Community. Perhaps it has improved or I never dig deep enough.
I’d be at a complete loss for any obscure Windows issue though.